Great Barrington (37 min) | Lee (22 min) | Lenox (15 min) | North Adams & Williamstown (39/33 min) | Stockbridge (26 min)

*Average drive times from Pittsfield to other town centers

Famous For...

• Largest city in Berkshires

• Home to renowned museum and performing arts center

• Host of First Fridays Artswalk

• Cinemas, theaters and studios

• Diverse downtown storefronts, galleries and shops  

About Pittsfield

Pittsfield enjoys the distinction as the "City of Festivals." Perfectly placed in the heart of the Berkshires, this surprising haven bustles with cultural and recreational amenities. The first county agricultural fair in America was held here in 1810, perhaps portending its current-day reputation for celebrations. You'll discover many and varied concert series, art, culture, night life, fine and fun dining, charming lodgings, a professional baseball team, a multitude of parks and plenty of hometown celebrations and parades. Pittsfield embraces summer with an exciting Third Thursday celebration each month. The celebration includes countless arts and crafts, food vendors, Arts exhibitions, and other attractions. Among other venues are top-quality exhibitions at the Berkshire Museum, which houses American landscape paintings and an inspiring collection of Americana; and historical and cultural programming at Arrowhead, headquarters of the Berkshire County Historical Society and former home of author Herman Melville.

Find in Pittsfield

Stay & Plan

  • Yankee Inn FireSpa Suite

    Getaway To The Berkshires!

    This 100% solar powered, family owned & operated hotel in Lenox is the perfect spot to getaway with the family! Read more

  • Black Swan Inn

    Lakeside R&R

    Stay on the waterfront with gorgeous views of Laurel Lake Read more

  • Courtyard Lenox bar.jpg

    Drink, Dine, Decompress

    What better way to end your long day than with a cocktail and appetizer... in bed! the Courtyard by Marriott Lenox offers every convenience under one roof! Read more

  • Courtyard Marriott Lenox Girlfriend Getaway

    Girlfriend Getaway

    The Berkshires is the perfect place for a girlfriends notch shopping, amazing restaurants and comfortable lodging. Read more

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